2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid

Base Information

• Chemical Name: 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid
• CAS No.: 150013-59-5
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47

Synonyms:2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid

Chemical Property of 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid

Chemical Property:

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Technology Process of 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid

There total 12 articles about 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid benzyl ester (150013-58-4) → 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid (150013-59-5)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In ethyl acetate; under 760 Torr;

DOI:10.1021/jm00062a013

Reference yield:

7-oxabicyclo<2.2.1>heptane tetrahydrofuranol (404575-34-4) → 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid (150013-59-5)

Guidance literature:

Multi-step reaction with 11 steps

1: EtMgBr / tetrahydrofuran / 0 - 25 °C

2: H₂, AcOH / 20percent Pd(OH)2-C / 760 Torr

3: pyridine / 0 - 25 °C

4: n-Bu₄NF / tetrahydrofuran / 25 °C

5: 1.) Dess-Martin periodinane, 2.) K₂CO₃, NIS / 1.) CH₂Cl₂, 25 deg C, 2.) 25 deg C

6: K₂CO₃, MeOH / 25 °C

7: CrO₃, H₂SO₄ / acetone / 25 °C

8: 1-hydroxybenzotriazole, Et₃N, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 0 - 25 °C

9: PPh₃, CCl₄, (iPr)2NEt / acetonitrile; CH₂Cl₂ / 25 °C

10: CuBr₂, DBU / ethyl acetate; CHCl₃ / 25 °C

11: H₂ / 20percent Pd(OH)2-C / ethyl acetate / 760 Torr

With pyridine; chromium(VI) oxide; methanol; tetrachloromethane; N-iodo-succinimide; sulfuric acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(ll) bromide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jm00062a013

Reference yield:

C19H33BrMgOSi → 2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid (150013-59-5)

Guidance literature:

Multi-step reaction with 11 steps

1: EtMgBr / tetrahydrofuran / 0 - 25 °C

2: H₂, AcOH / 20percent Pd(OH)2-C / 760 Torr

3: pyridine / 0 - 25 °C

4: n-Bu₄NF / tetrahydrofuran / 25 °C

5: 1.) Dess-Martin periodinane, 2.) K₂CO₃, NIS / 1.) CH₂Cl₂, 25 deg C, 2.) 25 deg C

6: K₂CO₃, MeOH / 25 °C

7: CrO₃, H₂SO₄ / acetone / 25 °C

8: 1-hydroxybenzotriazole, Et₃N, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 0 - 25 °C

9: PPh₃, CCl₄, (iPr)2NEt / acetonitrile; CH₂Cl₂ / 25 °C

10: CuBr₂, DBU / ethyl acetate; CHCl₃ / 25 °C

11: H₂ / 20percent Pd(OH)2-C / ethyl acetate / 760 Torr

With pyridine; chromium(VI) oxide; methanol; tetrachloromethane; N-iodo-succinimide; sulfuric acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(ll) bromide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jm00062a013

upstream raw materials:

2-{(1R,2S,3R,4S)-3-[2-(2-Methoxycarbonyl-2-methyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid benzyl ester

7-oxabicyclo<2.2.1>heptane tetrahydrofuranol

3-[2-((1S,2R,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-2,2-dimethyl-propionic acid methyl ester

Acetic acid (1R,2R,3R,4S)-3-[2-(3-hydroxy-2,2-dimethyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl ester

Downstream raw materials:

3-{2-[(1S,2R,3S,4R)-3-(4-Chlorocarbonyl-oxazol-2-yl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-2,2-dimethyl-propionic acid methyl ester

3-(2-{(1S,2R,3S,4R)-3-[4-(4-Cyclohexyl-butylcarbamoyl)-oxazol-2-yl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-2,2-dimethyl-propionic acid methyl ester

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